EP3466925A1 - Substituierte oder unsubstituierte allylgruppe enthaltende maleimidverbindung, herstellungsverfahren dafür sowie zusammensetzung und gehärtetes produkt mit verwendung der besagten verbindung - Google Patents
Substituierte oder unsubstituierte allylgruppe enthaltende maleimidverbindung, herstellungsverfahren dafür sowie zusammensetzung und gehärtetes produkt mit verwendung der besagten verbindung Download PDFInfo
- Publication number
- EP3466925A1 EP3466925A1 EP17806786.4A EP17806786A EP3466925A1 EP 3466925 A1 EP3466925 A1 EP 3466925A1 EP 17806786 A EP17806786 A EP 17806786A EP 3466925 A1 EP3466925 A1 EP 3466925A1
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- European Patent Office
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- compound
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- resin
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- -1 maleimide compound Chemical class 0.000 title claims abstract description 189
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 title claims abstract description 128
- 239000000203 mixture Substances 0.000 title claims description 219
- 150000001875 compounds Chemical class 0.000 title claims description 77
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 239000000463 material Substances 0.000 claims abstract description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 46
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims abstract description 35
- 239000004065 semiconductor Substances 0.000 claims abstract description 17
- 239000012776 electronic material Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000003277 amino group Chemical group 0.000 claims description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
- 239000000945 filler Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000011889 copper foil Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 239000003779 heat-resistant material Substances 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 144
- 239000011347 resin Substances 0.000 abstract description 144
- 239000003822 epoxy resin Substances 0.000 abstract description 33
- 229920000647 polyepoxide Polymers 0.000 abstract description 33
- 229920003192 poly(bis maleimide) Polymers 0.000 abstract description 18
- 238000005979 thermal decomposition reaction Methods 0.000 abstract description 11
- 229920006015 heat resistant resin Polymers 0.000 abstract description 3
- 238000011835 investigation Methods 0.000 abstract description 3
- 229920001568 phenolic resin Polymers 0.000 abstract description 3
- 239000005007 epoxy-phenolic resin Substances 0.000 abstract description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 89
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
- 238000001723 curing Methods 0.000 description 53
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 230000000052 comparative effect Effects 0.000 description 37
- 239000004643 cyanate ester Substances 0.000 description 37
- 239000000835 fiber Substances 0.000 description 32
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 30
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 28
- 239000010419 fine particle Substances 0.000 description 27
- 238000000465 moulding Methods 0.000 description 27
- 239000003795 chemical substances by application Substances 0.000 description 24
- 229920003986 novolac Polymers 0.000 description 23
- 238000010348 incorporation Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 19
- 239000002184 metal Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- 238000000576 coating method Methods 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 17
- 239000000377 silicon dioxide Substances 0.000 description 17
- 239000012295 chemical reaction liquid Substances 0.000 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 239000002245 particle Substances 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 13
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 13
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 13
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 13
- 238000000113 differential scanning calorimetry Methods 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 13
- 238000005452 bending Methods 0.000 description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000003475 lamination Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000011342 resin composition Substances 0.000 description 8
- 238000004611 spectroscopical analysis Methods 0.000 description 8
- SCZZNWQQCGSWSZ-UHFFFAOYSA-N 1-prop-2-enoxy-4-[2-(4-prop-2-enoxyphenyl)propan-2-yl]benzene Chemical compound C=1C=C(OCC=C)C=CC=1C(C)(C)C1=CC=C(OCC=C)C=C1 SCZZNWQQCGSWSZ-UHFFFAOYSA-N 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
- 238000001514 detection method Methods 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 239000003365 glass fiber Substances 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000011888 foil Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000013034 phenoxy resin Substances 0.000 description 6
- 229920006287 phenoxy resin Polymers 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910000679 solder Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000001029 thermal curing Methods 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 5
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 5
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 5
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 4
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920000049 Carbon (fiber) Polymers 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 150000003934 aromatic aldehydes Chemical class 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
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- 238000006297 dehydration reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
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- 125000005647 linker group Chemical group 0.000 description 4
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- 238000005259 measurement Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000004917 carbon fiber Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 239000012784 inorganic fiber Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
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- B32B2307/00—Properties of the layers or laminate
- B32B2307/50—Properties of the layers or laminate having particular mechanical properties
- B32B2307/546—Flexural strength; Flexion stiffness
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/12—Mountings, e.g. non-detachable insulating substrates
- H01L23/14—Mountings, e.g. non-detachable insulating substrates characterised by the material or its electrical properties
- H01L23/145—Organic substrates, e.g. plastic
Definitions
- the present invention relates to a substituted or unsubstituted allyl group-containing maleimide compound, a method for production thereof, and a composition and a cured product produced using the compound.
- prepregs obtainable by impregnating glass clothes with thermosetting resins such as an epoxy resin, a benzoxazine resin, and a BT (bismaleimide-triazine) resin, heating and drying the impregnated glass clothes; laminated plates obtained by heating and curing the prepregs; and multilayer plates obtained by combining the laminated plates and the prepregs and heating and curing the combinations, are widely used.
- thermosetting resins such as an epoxy resin, a benzoxazine resin, and a BT (bismaleimide-triazine) resin
- BMI bismaleimides
- DDM 4,4'-diaminodiphenylmethane
- DDE 4,4'-diaminodiphenyl ether
- Patent Literature 1 JP-A-2015-193628
- BMI's are conventionally known as highly heat-resistant resins; however, there is a demand for a resin having superior heat resistance for advanced material applications and the like.
- the inventors of the present invention conducted a thorough investigation, and as a result, the inventors found that the problem described above can be solved by a substituted or unsubstituted allyl group-containing maleimide compound having a structure with three or more benzene rings and having one or more substituted or unsubstituted allyl groups as well as one or more maleimide groups.
- this invention relates to a substituted or unsubstituted allyl group-containing maleimide compound, which is a compound having a structure with three or more benzene rings, having one or more groups each having a substituted or unsubstituted allyl group, and having one or more maleimide groups.
- a substituted or unsubstituted allyl group-containing maleimide compound having superior heat resistance is provided.
- the substituted or unsubstituted allyl group-containing maleimide compound can be suitably used for use applications such as heat-resistant members and electronic members, particularly a semiconductor encapsulating material, a circuit board, a buildup film, a buildup substrate, an adhesive, a resist material, a matrix resin for a fiber-reinforced resin, a highly heat-resistant prepreg, and a resin for a heat-resistant coating material.
- the substituted or unsubstituted allyl group-containing maleimide compound of the invention has a structure with three or more benzene rings, has one or more groups each having a substituted or unsubstituted allyl group, and has one or more maleimide groups.
- the substituted or unsubstituted allyl group-containing maleimide compound has the above-described configuration, superior heat resistance can be realized compared to conventional maleimide compounds. Particularly, when the substituted or unsubstituted allyl group-containing maleimide compound has three or more benzene rings, the thermal decomposition resistance temperature can be increased.
- the substituted or unsubstituted allyl group-containing maleimide compound may have a low melting point.
- maleimide compounds Since conventional maleimide compounds have high melting points and do not melt at low temperatures, these maleimide compounds have poor handleability. Furthermore, for example, even if conventional maleimide compounds are incorporated into curable resins, since compatibility is markedly poor, various components react and cure locally, and therefore, uniform cured products cannot be produced. This has been one of the factors limiting the use applications of maleimide compounds.
- the substituted or unsubstituted allyl group-containing maleimide compound has a low melting point, the compound has high handleability. Furthermore, for example, the maleimide compound has excellent compatibility with a curable resin in a curable resin, and a uniform composition can be produced. Thus, it is possible to produce a cured product suitably.
- the reason why the substituted or unsubstituted allyl group-containing maleimide compound has excellent solvent solubility is not necessarily clearly understood; however, it is speculated to be because the substituted or unsubstituted allyl group in the structure alleviates the crystallinity originating from aromatic ring.
- the substituted or unsubstituted allyl group-containing maleimide compound also has excellent solvent solubility.
- the maleimide compound can also be used in the form of a coating liquid or the like.
- the maleimide compound can be suitably applied to use applications such as a resin for a heat-resistant coating material, to which conventional maleimide compounds cannot be applied.
- the substituted or unsubstituted allyl group-containing maleimide compound of the invention has a structure with three or more benzene rings.
- the benzene rings may or may not have a substituent, and the mode of bonding is not particularly limited.
- the benzene rings may be linked directly to one another or may be linked through linking groups, or it is still acceptable that the benzene rings are fused with one another and form a fused ring.
- Preferred examples of the structure having three or more benzene rings include structures of the following Formulae (1-1) to (1-11).
- the benzene rings may each have a substituent.
- examples of the substituent for the benzene rings include, but are not limited to, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylcarbonyl group having 2 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, an alkylcarbonyloxy group having 2 to 10 carbon atoms, a halogen atom, a hydroxyl group, an amino group, an amide group, a ureido group, a urethane group, a carboxyl group, a thioether group, a cyano group, and a nitro group.
- alkyl group having 1 to 10 carbon atoms examples include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a cyclobutyl group, a pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a hexyl group, a cyclohexyl group, a nonyl group, and a decyl group.
- alkenyl group having 2 to 10 carbon atoms examples include, but are not limited to, a vinyl group, an allyl group, a propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.
- alkynyl group having 2 to 10 carbon atoms examples include, but are not limited to, an ethynyl group, a propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-hexynyl group, a 2-hexynyl group, a 3-hexynyl group, a 4-hexynyl group, and a 5-hexynyl group.
- aryl group having 6 to 10 carbon atoms examples include, but are not limited to, a phenyl group and a naphthyl group.
- alkoxy group having 1 to 10 carbon atoms examples include, but are not limited to, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, a pentyloxy group, a hexyloxy group, and a cyclohexyloxy group.
- alkylcarbonyl group having 2 to 10 carbon atoms examples include, but are not limited to, a methylcarbonyl group, an ethylcarbonyl group, a propylcarbonyl group, an isopropylcarbonyl group, a butylcarbonyl group, a pentylcarbonyl group, a hexylcarbonyl group, a cyclohexylcarbonyl group, and a nonylcarbonyl group.
- alkyloxycarbonyl group having 2 to 10 carbon atoms examples include, but are not limited to, a methyloxycarbonyl group, an ethyloxycarbonyl group, a propyloxycarbonyl group, a butyloxycarbonyl group, a hexyloxycarbonyl group, and a cyclohexyloxycarbonyl group.
- alkylcarbonyloxy group having 2 to 10 carbon atoms examples include, but are not limited to, a methylcarbonyloxy group, an ethylcarbonyloxy group, a propylcarbonyloxy group, a butylcarbonyloxy group, a hexylcarbonyloxy group, and a cyclohexylcarbonyloxy group.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- each of the benzene rings may have the above-mentioned substituents singly or in combination of two or more kinds thereof.
- X 1 to X 10 described above each independently represent a direct bond, a hydrocarbon group having 1 to 3 carbon atoms which may have a substituent, an oxygen atom, a sulfur atom, or a sulfonyl group.
- X 1 to X 10 are each a divalent linking group.
- hydrocarbon group having 1 to 3 carbon atoms examples include methylene, ethylene, and propylene.
- examples of the substituent for the hydrocarbon group include an alkyl group having 1 to 5 carbon atoms, such as a methyl group, an ethyl group, a propyl group, or a butyl group; and a halogenated alkyl group having 1 to 5 carbon atoms, such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a chloromethyl group, a dichloromethyl group, a trichloromethyl group, a bromomethyl group, a dibromomethyl group, a tribromomethyl group, a chlorofluoromethyl group, or a pentafluoroethyl group.
- an alkyl group having 1 to 5 carbon atoms such as a methyl group, an ethyl group, a propyl group, or a butyl group
- a halogenated alkyl group having 1 to 5 carbon atoms such as a fluoromethyl group
- X 1 to X 10 are each preferably a direct bond, a hydrocarbon group having one carbon atom, an oxygen atom, or a sulfur atom.
- Y described above represents a carbon atom which may have a substituent, or a nitrogen atom.
- examples of the substituent that can be carried by the carbon atom are the same as the examples of the substituent of the hydrocarbon group as described above.
- Y is a trivalent or tetravalent linking group, and preferably a trivalent linking group.
- structures of Formulae (1-4), (1-5), (1-8), (1-9), (1-10), and (1-11) are preferred; structures of Formulae (1-5), (1-8), and (1-10) are more preferred; structures of the following Formulae (1-5-1), (1-5-2), (1-8-1), and (1-8-2) are even more preferred; and structures of the following Formulae (1-8-1) and (1-8-2) are particularly preferred.
- the benzene rings may each have a substituent.
- examples of the substituent are the same as the examples of the above-mentioned substituent of the benzene ring.
- the substituted or unsubstituted allyl group-containing maleimide compound of the invention may have only one of the structures represented by Formulae (1-1) to (1-11), or may have two or more thereof. According to an embodiment, it is preferable that the substituted or unsubstituted allyl group-containing maleimide compound has three to five benzene rings, and more preferably three to four benzene rings, in the structure. When the number of benzene rings in the structure is 3 or larger, the maleimide compound has excellent heat resistance, which is preferable. Meanwhile, when the number of benzene rings in the structure is 5 or less, the molecular structure becomes compact, and therefore, the melting point is not too high, while the maleimide compound has excellent handleability, which is preferable.
- Preferred examples of the structure having three or more benzene rings include structures represented by the following formulae.
- the structure having three or more benzene rings may have a substituent to the extent that the effects of the invention are not impaired.
- substituent include the above-mentioned examples of the substituent of the benzene ring.
- the benzene rings may have the substituents singly or in combination of two or more kinds thereof.
- more preferred examples of the structure having three or more benzene rings include structures represented by the following formulae.
- particularly preferred examples of the structure having three or more benzene rings include structures represented by the following formulae.
- the substituted or unsubstituted allyl group-containing maleimide compound of the invention has one or more groups each having a substituted or unsubstituted allyl group and further has one or more maleimide groups.
- substituted or unsubstituted allyl group means an allyl group, or a group in which at least one of hydrogen atoms bonded to the carbon atoms constituting a double bond of an allyl group has been substituted by a methyl group.
- examples of the substituted or unsubstituted allyl group include groups represented by the following structural formulae.
- the symbol "*" represents a site that is bonded to another group.
- examples of the substituted or unsubstituted allyl group preferably include groups represented by structural formulae.
- the group having a substituted or unsubstituted allyl group and the maleimide group are usually bonded directly to benzene rings in the structure having three or more benzene rings.
- the maleimide group and the group containing a substituted or unsubstituted allyl group exist on the same benzene ring, because heat resistance is further enhanced.
- the numbers of the groups containing a substituted or unsubstituted allyl group and the maleimide groups are preferably such that there are two groups containing a substituted or unsubstituted allyl group and one maleimide group; one group containing a substituted or unsubstituted allyl group and two maleimide groups; or two groups containing a substituted or unsubstituted allyl group and two maleimide groups. It is more preferable that there are two groups containing a substituted or unsubstituted allyl group and one maleimide group; or two groups containing a substituted or unsubstituted allyl group and two maleimide groups . It is even more preferable that there are two groups containing a substituted or unsubstituted allyl group and two maleimide groups.
- the substituted or unsubstituted allyl group-containing maleimide compound is preferably represented by the following Formula (2).
- n and m each independently represent an integer from 1 to 5, more preferably 1 to 4, even more preferably 1 or 2, and particularly preferably 2.
- m : n 1 : 5 to 5 : 1, preferably 1 : 2 to 2 : 1, and more preferably 1 : 1.
- Aly represents a group containing a substituted or unsubstituted allyl group represented by the following Formula (3) .
- Z represents a direct bond, or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent; and R 1 , R 2 , and R 3 each independently represent a hydrogen atom or a methyl group.
- hydrocarbon group having 1 to 10 carbon atoms examples include an alkylene group, an alkenylene group, an alkynylene group, a cycloalkylene group, an arylene group, and groups combining a plurality of those.
- alkylene group examples include a methylene group, a methyne group, an ethylene group, a propylene group, a butylene group, a pentylene group, and a hexylene group.
- alkenylene group examples include a vinylene group, a 1-methylvinylene group, a propenylene group, a butenylene group, and a pentenylene group.
- alkynylene group examples include an ethynylene group, a propynylene group, a butynylene group, a pentynylene group, and a hexynylene group.
- cycloalkylene group examples include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, and a cyclohexylene group.
- arylene group examples include a phenylene group, a tolylene group, a xylylene group, and a naphthylene group.
- Z is preferably a direct bond or methylene, and more preferably a direct bond.
- Aly is represented by any one of the following structural formulae.
- MI represents a maleimide group represented by the following Formula (4).
- R 4 and R 5 each independently represent a hydrogen atom or a methyl group.
- the maleimide group and the group containing a substituted or unsubstituted allyl group exist on the same benzene ring, because heat resistance is further enhanced.
- A represents a structure having three or more benzene rings.
- the structure having three or more benzene rings is similar to the structure described above.
- Preferred examples of the structure of the allyl group-containing maleimide compound of the invention include structures represented by the following Formulae (5-1) to (5-33).
- structures represented by Formulae (5-1) to (5-22) and (5-30) to (5-33) are preferred; structures represented by Formulae (5-1) to (5-7), (5-12) to (5-18), and (5-30) to (5-33) are more preferred; structures represented by Formulae (5-1), (5-3) to (5-5), (5-12), (5-13), (5-15), (5-16), and (5-30) to (5-33) are even more preferred; structures represented by Formulae (5-1), (5-3), (5-12), (5-14), and (5-30) to (5-33) are particularly preferred; and structures represented by Formulae (5-1), (5-3), (5-12), and (5-14) are most preferred.
- the method for producing a substituted or unsubstituted allyl group-containing maleimide compound of the invention is not particularly limited; however, production can be carried out efficiently by implementing the following steps:
- the substituted or unsubstituted allyl group-containing maleimide compound according to the invention can be efficiently produced by a production method including the above-described steps.
- the substituted or unsubstituted allyl group-containing maleimide compound of the invention which is a compound having a structure with three or more benzene rings, having one or more groups having a substituted or unsubstituted allyl group, and having one or more maleimide groups, can be produced.
- the hydroxyl group-containing aromatic amino compound having three or more benzene rings is preferably a compound having the structure represented by Formula (1-1) or (1-2), a hydroxyl group, and an amino group.
- Specific examples include, but are not limited to, conventionally known compounds such as 9,9-bis(3-amino-4-hydroxyphenyl)fluorene, 1,3-bis(4-amino-3-hydroxyphenoxy)benzene, and 4,4'-diamino-4"-hydroxytriphenylamine.
- examples of the method for producing the hydroxyl group-containing aromatic amino compound having three or more benzene rings include a method of nitrating a hydroxyl group-containing aromatic compound and then reducing the resultant; a method of reacting a hydroxyl group-containing aromatic compound with a nitro group-containing aromatic aldehyde and then reducing the reaction product; and a method of reacting an amino group-containing aromatic compound with a hydroxyl group-containing aromatic aldehyde.
- a method of reacting an amino group-containing aromatic compound with a methoxy group-containing aromatic aldehyde or a method of reacting an amino group- and methoxy group-containing aromatic compound with an aromatic aldehyde, subsequently deprotecting a methoxy group, and converting the methoxy group into a hydroxyl group, may also be used.
- Protection of an amino group in step 1-1) may be carried out using a conventionally known method, and for example, an amino group can be protected by acetylating the amino group.
- any conventionally known acetylating agent may be used, and examples of the agent include acetic anhydride and acetyl chloride.
- a substituted or unsubstituted allyl group can be introduced by, for example, reacting a hydroxyl group of a hydroxyl group-containing aromatic amino compound having a protected amino group with a halide of a substituted or unsubstituted allyl group-containing compound in the presence of a base.
- Examples of the halide of a substituted or unsubstituted allyl group-containing compound include allyl bromide, methallyl bromide (3-bromo-2-methyl-1-propene), allyl chloride, methallyl chloride (3-chloro-2-methyl-1-propene), cis-1-chloro-2-butene, trans-1-chloro-2-butene, 1-chloro-3-methyl-2-butene, and 1-bromo-3-methyl-2-butene.
- examples of the base include potassium carbonate.
- step 1-3) and step 1-4 the protected amino group is deprotected, and that amino group is maleimidated.
- Maleimidation of the amino group can be achieved by, for example, reacting the amino group with a compound represented by the following Formula (6).
- R 4 and R 5 each independently represent a hydrogen atom or a methyl group.
- Examples of the compound represented by Formula (6) include maleic anhydride, citraconic anhydride, and 2,3-dimethylmaleic anhydride.
- the substituted or unsubstituted allyl group-containing maleimide compound of the invention which is a compound having a structure with three or more benzene rings, having one or more groups each having a substituted or unsubstituted allyl group, and having one or more maleimide groups, can be produced.
- unreacted monomers may remain in the reaction system, or other compounds that are different from the substituted or unsubstituted allyl group-containing maleimide compound may be produced as products.
- the other compounds include non-cyclized amic acid, isoimide, monomers, and an oligomer of a product.
- the substances may be eliminated by implementing purification processes, or depending on the use application, the maleimide compound may be used while having those substances incorporated therein.
- composition of the invention includes the substituted or unsubstituted allyl group-containing maleimide compound of the invention.
- the substituted or unsubstituted allyl group-containing maleimide compound according to the invention has excellent heat resistance
- a cured product obtainable by curing a composition including this compound has excellent resistance to thermal decomposition, has a high glass transition temperature, and undergoes low linear expansion
- the cured product can be suitably used for heat-resistant members or electronic members.
- the substituted or unsubstituted allyl group-containing maleimide compound has a low melting point and exhibits low melting viscosity. Therefore, according to a preferred embodiment, a composition including a substituted or unsubstituted allyl group-containing maleimide compound and a resin is provided. This composition can be suitably applied particularly to semiconductor encapsulating material applications and the like.
- the substituted or unsubstituted allyl group-containing maleimide compound has solvent solubility, too. Therefore, according to a preferred embodiment, a composition including the substituted or unsubstituted allyl group-containing maleimide compound and a dispersing medium is provided. This composition can be suitably applied to heat-resistant coating material applications and the like.
- composition of the present invention may include a reactive compound as a compounding substance in addition to the substituted or unsubstituted allyl group-containing maleimide compound of the invention.
- a reactive compound as a compounding substance in addition to the substituted or unsubstituted allyl group-containing maleimide compound of the invention.
- the reactive compound as used herein is a compound having a reactive group, and this compound may be a monomer, an oligomer, or a polymer.
- the reactive group may be a functional group that does not react with the substituted or unsubstituted allyl group-containing maleimide compound of the invention or may be a functional group that reacts with the maleimide compound.
- the reactive group is preferably a functional group that reacts with the substituted or unsubstituted allyl group-containing maleimide compound of the invention.
- Examples of the functional group that reacts with the allyl group-containing maleimide compound of the invention include an epoxy group, a cyanato group, a maleimide group, a phenolic hydroxyl group, an oxazine ring, an amino group, and a group having a carbon-carbon double bond.
- Examples of a compound having an epoxy group include an epoxy resin and a phenoxy resin.
- Examples of a compound having a cyanato group include a cyanate ester resin.
- Examples of a compound having a maleimide group include a maleimide resin and a bismaleimide resin.
- Examples of a compound having a phenolic hydroxyl group include a phenol novolac resin, a cresol novolac resin, a dicyclopentadiene-modified phenolic resin, a phenol aralkyl resin, a naphthol aralkyl resin, and a biphenyl aralkyl resin.
- Examples of a compound having an oxazine ring include benzoxazine obtainable by reacting a phenolic compound or an aromatic amino compound with formaldehyde. These phenolic compound and aromatic amino compound may have a reactive functional group in the structure.
- Examples of a compound having an amino group include aromatic amino compounds such as DDM (4,4'-diaminodiphenylmethane), DDE (4,4'-diaminodiphenyl ether), 3,4'-diaminodiphenyl ether, 2,2- ⁇ bis4-(4-aminophenoxy)phenyl ⁇ propane, and 4,4'-bis(4-aminophenoxy)biphenyl.
- aromatic amino compounds such as DDM (4,4'-diaminodiphenylmethane), DDE (4,4'-diaminodiphenyl ether), 3,4'-diaminodiphenyl ether, 2,2- ⁇ bis4-(4-aminophenoxy)phenyl ⁇ propane, and 4,4'-bis(4-aminophenoxy)biphenyl.
- Examples of a compound having a group having a carbon-carbon double bond include a maleimide compound, a vinylic compound, and a (meth)allylic compound.
- maleimide compound when a compound is described simply as "maleimide compound”, this means that the compound is a maleimide compound other than the substituted or unsubstituted allyl group-containing maleimide compound according to the invention.
- (meth) allylic compound when a compound is described simply as " (meth) allylic compound”, this means that the compound is a (meth) allylic compound other than the substituted or unsubstituted allyl group-containing maleimide compound according to the invention.
- the above-described reactive compounds may have only one kind of reactive group, or may have a plurality of kinds of reactive groups.
- the number of functional groups may also be one or a plurality. Furthermore, it is also acceptable to use a plurality of kinds of reactive compounds at the same time.
- Preferred examples of the reactive compound include an epoxy resin, a phenoxy resin, a cyanate ester resin, a maleimide compound, a vinylic compound, and an aromatic amino compound.
- particularly preferred examples include a maleimide compound, a cyanate ester resin, an epoxy resin, and an aromatic amino compound.
- a maleimide compound acquires an increased crosslinking density as a result of a self-addition reaction between the substituted or unsubstituted allyl group-containing maleimide compound and maleimide groups, or an ene reaction between an allyl group and a maleimide group. As the result, heat resistance, and particularly the glass transition temperature, is enhanced.
- a cured product obtained from a cyanate ester resin and the substituted or unsubstituted allyl group-containing maleimide compound of the invention exhibits excellent dielectric characteristics.
- An aromatic amino compound acquires an increased crosslinking density as a result of a Michael addition reaction between an amino group and a maleimide group, and the thermal decomposition resistance temperature and the glass transition temperature are increased.
- the epoxy resin is not particularly limited as long as the resin has epoxy groups, and examples include a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a bisphenol E type epoxy resin, a bisphenol S type epoxy resin, a bisphenol sulfide type epoxy resin, a phenylene ether type epoxy resin, a naphthylene ether type epoxy resin, a biphenyl type epoxy resin, a tetraethylbiphenyl type epoxy resin, a polyhydroxynaphthalene type epoxy resin, a phenol novolac type epoxy resin, a cresol novolac type epoxy resin, a triphenylmethane type epoxy resin, a tetraphenylethane type epoxy resin, a dicyclopentadiene-phenol addition reaction type epoxy resin, a phenol aralkyl type epoxy resin, a naphthol novolac type epoxy resin, a naphthol aralkyl type epoxy resin, a naphthol-phenol co-con
- a phenoxy resin is a high-molecular weight thermoplastic polyether resin based on diphenol and epihalohydrin such as epichlorohydrin, and a phenoxy resin having a weight average molecular weight of 20,000 to 100,000 is preferred.
- a phenoxy resin having one or more skeletons selected from a bisphenol A skeleton, a bisphenol F skeleton, a bisphenol S skeleton, a bisphenol acetophenone skeleton, a novolac skeleton, a biphenyl skeleton, a fluorene skeleton, a dicyclopentadiene skeleton, a norbornene skeleton, a naphthalene skeleton, an anthracene skeleton, an adamantine skeleton, a terpene skeleton, and a trimethylcyclohexane skeleton, may be used.
- cyanate ester resin examples include a bisphenol A type cyanate ester resin, a bisphenol F type cyanate ester resin, a bisphenol E type cyanate ester resin, a bisphenol S type cyanate ester resin, a biphenol sulfide type cyanate ester resin, a phenylene ether type cyanate ester resin, a naphthylene ether type cyanate ester resin, a biphenyl type cyanate ester resin, a tetramethyl biphenyl type cyanate ester resin, a polyhydroxynaphthalene type cyanate ester resin, a phenol novolac type cyanate ester resin, a cresol novolac type cyanate ester resin, a triphenylmethane type cyanate ester resin, a tetraphenylethane type cyanate ester resin, a dicyclopentadiene-phenol addition reaction type cyanate ester resin, a phenol a
- cyanate ester resins particularly from the viewpoint that a cured product having excellent heat resistance is obtained, it is preferable to use a bisphenol A type cyanate ester resin, a bisphenol F type cyanate ester resin, a bisphenol E type cyanate ester resin, a polyhydroxynaphthalene type cyanate ester resin, a naphthylene ether type cyanate ester resin, or a novolac type cyanate ester resin. From the viewpoint that a cured product having excellent dielectric characteristics is obtained, a dicyclopentadiene-phenol addition reaction type cyanate ester resin is preferred.
- examples include various compounds represented by any of the following Structural Formulae (i) to (iii).
- R represents an s-valent organic group
- ⁇ and ⁇ each represent any one of a hydrogen atom, a halogen atom, an alkyl group, and an aryl group
- s represent an integer of 1 or greater.
- R represents any one of a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, a halogen atom, a hydroxyl group, and an alkoxy group; s represents an integer from 1 to 3; and t represents the average number of the repeating units and is from 0 to 10.
- R represents any one of a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, a halogen atom, a hydroxyl group, and an alkoxy group; s represents an integer from 1 to 3; and t represents the average number of the repeating units and is from 0 to 10.
- maleimide compounds may be used singly, or two or more kinds thereof may be used in combination.
- oxazine compound examples include, but are not limited to, a reaction product of bisphenol F, formalin, and aniline (F-a type benzoxazine resin); a reaction product of 4,4'-diaminodiphenylmethane, formalin, and phenol (P-d type benzoxazine resin) ; a reaction product of bisphenol A, formalin, and aniline; a reaction product of dihydroxydiphenyl ether, formalin, and aniline; a reaction product of diaminodiphenyl ether, formalin, and phenol; a reaction product of a dicyclopentadiene-phenol addition type resin, formalin, and aniline; a reaction product of phenolphthalein, formalin, and aniline; and a reaction product of dihydroxydiphenyl sulfide, formalin, and aniline.
- F-a type benzoxazine resin a reaction product of 4,4'-diaminodiphenylmethane, formalin,
- Examples of the vinylic compound include alkyl (meth)acrylates having an alkyl group having 1 to 22 carbon atoms, such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and lauryl (meth)acrylate; aralkyl (meth)acrylates such as benzyl (meth)acrylate and 2-phenylethyl (meth)acrylate; cycloalkyl (meth)acrylates such as cyclohexyl (meth)acrylate and isobornyl (meth)acrylate; ⁇ -alkoxyalkyl (meth)acrylates such as 2-methoxyethyl (meth)acrylate and 4-methoxybutyl (meth)
- Examples of the (meth)allylic compound include allyl esters such as allyl acetate, allyl chloride, allyl caproate, allyl caprylate, allyl laurate, allyl palmitate, allyl stearate, allyl benzoate, allyl acetoacetate, and allyl lactate; allyloxy alcohols such as allyloxy methanol and allyloxy ethanol; compounds containing two allyl groups, such as diallyl phthalate, diallyl isophthalate, diallyl cyanurate, diallyl isocyanurate, pentaerythritol diallyl ether, trimethylolpropane diallyl ether, glycerin diallyl ether, bisphenol A diallyl ether, bisphenol F diallyl ether, ethylene glycol diallyl ether, diethylene glycol diallyl ether, triethylene glycol diallyl ether, propylene glycol diallyl ether, di
- a maleimide group and a substituted or unsubstituted allyl group both exist.
- the ratio of the maleimide group and the substituted or unsubstituted allyl group is not particularly limited; however, the ratio of the mole number of maleimide groups : mole number of substituted or unsubstituted allyl groups is preferably 1 : 10 to 10 : 1, and when the ratio is 1 : 5 to 5 : 1, it is preferable because heat resistance is excellent. Particularly, in the case of 1 : 2 to 2 : 1, it is preferable because the balance between heat resistance and the mixture viscosity is excellent.
- the "mole number of maleimide groups" and the "mole number of substituted or unsubstituted allyl groups” are calculated to include the mole numbers of the groups in compounds other than the substituted or unsubstituted allyl group-containing maleimide compound.
- composition of the invention may further include a filler, in addition to the substituted or unsubstituted allyl group-containing maleimide compound.
- a filler in addition to the substituted or unsubstituted allyl group-containing maleimide compound.
- the filler include inorganic fillers and organic fillers.
- the inorganic fillers include inorganic fine particles.
- the inorganic fine particles include, as fine particles having excellent heat resistance, particles of alumina, magnesia, titania, zirconia, and silica (quartz, fumed silica, precipitated silica, silicic anhydride, fused silica, crystalline silica, ultrafine powder amorphous silica, and the like); as fine particles capable of excellent thermal conduction, particles of boron nitride, aluminum nitride, alumina oxide, titanium oxide, magnesium oxide, zinc oxide, silicon oxide, and diamond; as particles having excellent electrical conductivity, metal fillers and/or metal-coated fillers using simple metals or alloys (for example, iron, copper, magnesium, aluminum, gold, silver, platinum, zinc, manganese, and stainless steel); as fine particles having excellent barrier properties, particles of minerals such as mica, clay, kaolin, talc, zeolite, wollastonite, and smectite, and particles of potassium titanate, magnesium sulfate, se
- inorganic fine particles may be selected as appropriate depending on the use application, and the inorganic fine particles may be used singly or in combination of a plurality of kinds thereof. Furthermore, since the above-mentioned inorganic fine particles also have various characteristics in addition to the characteristics listed as examples, the inorganic fine particles may be selected as appropriately according to the use applications.
- silica fine particles such as powdered silica or colloidal silica can be used without particular limitations.
- known silica fine particles such as powdered silica or colloidal silica can be used without particular limitations.
- commercially available silica fine particles in a powder form include AEROSIL 50 and 200 manufactured by Nippon Aerosil Co., Ltd.; SHIELDEX H31, H32, H51, H52, H121, and H122 manufactured by AGC Inc.; E220A and E220 manufactured by Nippon Silica Industrial Co., Ltd.; SYLYSIA A470 manufactured by FUJI SILYSIA CHEMICAL, LTD.; and SG FLAKE manufactured by Nippon Sheet Glass Co., Ltd.
- examples of commercially available colloidal silica include methanol silica sols, IPA-ST, MEK-ST, NBA-ST, XBA-ST, DMAC-ST, ST-UP, ST-OUP, ST-20, ST-40, ST-C, ST-N, ST-O, ST-50, and ST-OL, manufactured by Nissan Chemical Corporation.
- Surface-modified silica fine particles may also be used, and examples thereof include a product obtained by surface-treating the above-described silica fine particles with a reactive silane coupling agent having a hydrophobic group, and a product obtained by modifying the silica fine particles with a compound having a (meth)acryloyl group.
- a commercially available powdered silica that has been modified with a compound having a (meth)acryloyl group include AEROSIL RM50 and R711 manufactured by Nippon Aerosil Co., Ltd.
- examples of a commercially available colloidal silica that has been modified with a compound having a (meth)acryloyl group include MIBK-SD manufactured by Nissan Chemical Corporation.
- the shape of the silica fine particles is not particularly limited, and particles having a spherical shape, a hollow shape, a porous shape, a rod shape, a sheet shape, a fibrous shape, or an undefined shape can be used.
- the primary particle size is preferably in the range of 5 to 200 nm. When the primary particle size is 5 nm or more, the inorganic fine particles are suitably dispersed in the dispersion, and when the primary particle size is 200 nm or less, a decrease in the strength of the cured product can be prevented.
- titanium oxide fine particles not only an extender pigment but also an ultraviolet light-responsive photocatalyst can be used, and for example, anatase type titanium oxide, rutile type titanium oxide, or brookite type titanium oxide can be used. Furthermore, particles designed to respond to visible light by doping a heteroelement into the crystal structure of titanium oxide can also be used.
- an anionic element such as nitrogen, sulfur, carbon, fluorine, or phosphorus; or a cationic element such as chromium, iron, cobalt, or manganese is suitably used.
- a powder, a sol obtained by dispersing titanium oxide fine particles in an organic solvent or in water, or a slurry can be sued.
- Examples of commercially available titanium oxide fine particles in a powder form include AEROSIL P-25 manufactured by Nippon Aerosil Co., Ltd.; and ATM-100 manufactured by TAYCA CORPORATION. Furthermore, examples of commercially available titanium oxide fine particles in a slurry form include TKD-701 manufactured by TAYCA CORPORATION.
- composition of the invention may further include a fibrous substrate in addition to the substituted or unsubstituted allyl group-containing maleimide compound.
- the fibrous substrate of the invention is not particularly limited; however, a fibrous substrate that is used for fiber-reinforced resin is preferred, and inorganic fibers or organic fibers may be used.
- the inorganic fibers include inorganic fibers such as carbon fibers, glass fibers, boron fibers, alumina fibers, and silicon carbide fibers; mineral fibers such as carbon fibers, activated carbon fibers, graphite fibers, glass fibers, tungsten carbide fibers, silicon carbide fibers, ceramic fibers, alumina fibers, natural fibers, and basalt; boron fibers, boron nitride fibers, boron carbide fibers, and metal fibers.
- the metal fibers include aluminum fibers, copper fibers, brass fibers, stainless steel fibers, and steel fibers.
- organic fibers examples include synthetic fibers formed from resin materials such as polybenzazole, aramid, polyparaphenylene benzoxazole (PBO), polyester, acrylics, polyamide, polyolefin, polyvinyl alcohol, and polyallylate; natural fibers formed from cellulose, pulp, cotton, wool, and silk; and regenerated fibers such as proteins, polypeptides, and alginate.
- resin materials such as polybenzazole, aramid, polyparaphenylene benzoxazole (PBO), polyester, acrylics, polyamide, polyolefin, polyvinyl alcohol, and polyallylate
- natural fibers formed from cellulose, pulp, cotton, wool, and silk and regenerated fibers such as proteins, polypeptides, and alginate.
- carbon fibers and glass fibers are preferable because their range of industrial utilization is wider.
- only one kind thereof may be used, or a plurality of kinds thereof may be used at the same time.
- the fibrous substrate of the invention may be an aggregate of fibers, and the fibers may be in a continuous form or in a non-continuous form.
- the substrate may be a woven fabric or a non-woven fabric.
- the fibers may be in the form of a fiber bundle in which fibers are aligned in one direction, or may be in the form of a sheet in which fiber bundles are lined up.
- a three-dimensional shape obtained by providing a thickness to an aggregate of fibers may also be employed.
- the composition of the invention may also use a dispersing medium for the purpose of adjusting the solid content or viscosity of the composition.
- the dispersing medium may be a liquid medium that will not impair the effects of the invention, and examples include various organic solvents and liquid organic polymers.
- organic solvents examples include ketones such as acetone, methyl ethyl ketone (MEK), and methyl isobutyl ketone (MIBK); cyclic ethers such as tetrahydrofuran (THF) and dioxolane; esters such as methyl acetate, ethyl acetate, and butyl acetate; aromatics such as toluene and xylene; and alcohols such as carbitol, cellosolve, methanol, isopropanol, butanol, and propylene glycol monomethyl ether. These can be used singly or in combination; however, above all, methyl ethyl ketone is preferable from the viewpoints of volatility at the time of application and recovery of the solvent.
- ketones such as acetone, methyl ethyl ketone (MEK), and methyl isobutyl ketone (MIBK)
- cyclic ethers such as tetrahydr
- the liquid organic polymer is a liquid organic polymer that does not directly contribute to a curing reaction, and examples include a carboxyl group-containing polymer modification product (FLOWLEN G-900 and NC-500; KYOEISHA CHEMICAL Co., LTD.), an acrylic polymer (FLOWLEN WK-20; KYOEISHA CHEMICAL Co., LTD.), an amine salt of a special modified phosphoric acid ester (HIPLAAD ED-251; Kusumoto Chemicals, Ltd.), and a modified acrylic block copolymer (DISPERBYK 2000; BYK).
- a carboxyl group-containing polymer modification product FLOWLEN G-900 and NC-500
- KYOEISHA CHEMICAL Co., LTD. an acrylic polymer
- FLOWLEN WK-20 an acrylic polymer
- KYOEISHA CHEMICAL Co., LTD. an amine salt of a special modified phosphoric acid ester
- DISPERBYK 2000 DISPERBYK 2000;
- composition of the invention may have a resin other than the substituted or unsubstituted allyl group-containing maleimide compound of the invention.
- a resin any conventionally known resin may be incorporated to the extent that does not impair the effects of the invention, and for example, a thermosetting resin or a thermoplastic resin can be used.
- thermosetting resin is a resin having the characteristics by which the resin can change to be substantially insoluble and infusible when the resin is cured by means of heating, radiation, a catalyst, or the like. Specific examples thereof include a phenolic resin, a urea resin, a melamine resin, a benzoguanamine resin, an alkyd resin, an unsaturated polyester resin, a vinyl ester resin, a diallyl terephthalate resin, an epoxy resin, a silicone resin, a urethane resin, a furan resin, a ketone resin, a xylene resin, a thermosetting polyimide resin, a benzoxazine resin, an active ester resin, an aniline resin, a cyanate ester resin, a styrene-maleic anhydride (SMA) resin, and a maleimide resin other than the allyl group-containing maleimide compound obtainable by the invention.
- These thermosetting resins can be used singly or in combination of two or
- thermoplastic resin refers to a resin that can be melt-molded by heating. Specific examples thereof include a polyethylene resin, a polypropylene resin, a polystyrene resin, a rubber-modified polystyrene resin, an acrylonitrile-butadiene-styrene (ABS) resin, an acrylonitrile-styrene (AS) resin, a polymethyl methacrylate resin, an acrylic resin, a polyvinyl chloride resin, a polyvinylidenew chloride resin, a polyethylene terephthalate resin, an ethylene-vinyl alcohol resin, a cellulose acetate resin, an ionomer resin, a polyacrylonitrile resin, a polyamide resin, a polyacetal resin, a polybutylene terephthalate resin, a polylactic acid resin, a polyphenylene ether resin, a modified polyphenylene ether resin, a polycarbonate resin, a polysulfone resin,
- composition of the invention may use a curing agent in accordance with the compounding substances.
- a curing agent in accordance with the compounding substances.
- examples include various curing agents such as an amine-based curing agent, an amide-based curing agent, an acid anhydride-based curing agent, a phenolic curing agent, an active ester-based curing agent, a carboxyl group-containing curing agent, and a thiol-based curing agent.
- amine-based curing agent examples include diaminodiphenylmethane, diaminodiphenylethane, diaminodiphenyl ether, diaminodiphenylsulfone, ortho-phenylenediamine, meta-phenylenediamine, para-phenylenediamine, meta-xylenediamine, para-xylenediamine, diethyltoluenediamine, diethylenetriamine, triethylenetetramine, isophorone diamine, imidazole, a BF3-amine complex, a guanidine derivative, and a guanamine derivative.
- amide-based curing agent examples include dicyandiamide, and a polyamide resin synthesized from a dimer of linolenic acid and ethylenediamine.
- Examples of the acid anhydride-based curing agent include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, hexahydrophthalic anhydride, and methylhexahydrophthalic anhydride.
- phenolic curing agent examples include polyvalent phenolic compounds such as bisphenol A, bisphenol F, bisphenol S, resorcin, catechol, hydroquinone, fluorene bisphenol, 4,4'-biphenol, 4,4',4"-trihydroxytriphenylmethane, naphthalenediol, 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane, calixarene, a phenol novolac resin, a cresol novolac resin, an aromatic hydrocarbon formaldehyde resin-modified phenolic resin, a dicyclopentadiene-phenol addition type resin, a phenol aralkyl resin (Xylok resin), a polyvalent phenol novolac resin synthesized from a polyvalent hydroxy compound and formaldehyde, which is represented by a resorcin novolac resin, a naphthol aralkyl resin, a trimethylolmethane resin, a tetra
- These curing agents may be used singly or in combination of two or more kinds thereof.
- composition of the invention can also use a curing accelerator alone or in combination with the curing agent described above.
- a curing accelerator various compounds that accelerate a curing reaction of a curable resin can be used, and examples thereof include a phosphorus-based compound, a tertiary amine compound, an imidazole compound, an organic acid metal salt, a Lewis acid, and an amine complex salt.
- triphenylphosphine and tetraphenylphosphonium tetra-p-tolyl borate are preferred among the phosphorus-based compounds, and 1,8-diazabicyclo[5.4.0]-undecene (DBU) is preferred among tertiary amines.
- composition of the invention may also have other compounding substances.
- examples thereof include a catalyst, a polymerization initiator, an inorganic pigment, an organic pigment, an extender pigment, a clay mineral, a wax, a surfactant, a stabilizer, a fluidity adjusting agent, a coupling agent, a dye, a leveling agent, a rheology controlling agent, an ultraviolet absorber, an oxidation inhibitor, a flame retardant, and a plasticizer.
- a cured product obtainable by curing the composition of the invention undergoes low linear expansion and has a high glass transition temperature and excellent resistance to thermal decomposition, and therefore, the cured product can be used suitably for heat-resistant members or electronic members.
- the method for molding a cured product is not particularly limited, and the composition may be molded alone, or the composition may also be laminated on a base material to produce a laminate.
- the composition of the invention it is recommended to implement thermal curing.
- any conventionally known curing catalyst may be used; however, the composition of the invention can be cured even without using a curing catalyst, through a reaction between a maleimide group and an allyl group.
- the composition may be cured by heating for once, or the composition may be cured by performing multiple stages of a heating process.
- inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid
- organic acids such as p-toluenesulfonic acid, isopropyl monophosphate, and acetic acid
- inorganic bases such as sodium hydroxide and potassium hydroxide
- titanic acid esters such as tetraisopropyl titanate and tetrabutyl titanate
- various compounds containing basic nitrogen atoms such as 1,8-diazabicyclo[5.4.0]undecene-7 (DBU), 1,5-diazabicyclo[4.3.0]nonene-5 (DBN), 1,4-diazabicyclo[2.2.2]octane (DABCO), tri-n-butylamine, dimethylbenzylamine, monoethanolamine, imidazole, and 1-methylimidazole
- various quaternary ammonium salts such as a tetramethylammonium salt, a t
- the maleimide compound of the invention can also be used for curing by active energy rays in combination.
- a photopolymerization initiator may be incorporated into the composition.
- known agents may be used, and for example, one or more selected from the group consisting of acetophenones, benzyl ketals, and benzophenones can be preferably used.
- Examples of the acetophenones include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl) ketone.
- Examples of the benzyl ketals include 1-hydroxycyclohexyl-phenyl ketone and benzyl dimethyl ketal.
- Examples of the benzophenones include benzophenone and methyl o-benzoylbenzoate.
- Examples of the benzoins include benzoin, benzoin methyl ether, and benzoin isopropyl ether.
- the photopolymerization initiators may be used singly, or two or more kinds thereof may be used in combination.
- heating and active energy ray irradiation may be carried out simultaneously, or the two may be carried out separately.
- thermal curing may be carried out after active energy ray irradiation is carried out, or curing by active energy rays may be carried out after thermal curing.
- the respective curing methods may be carried out two or more times in combination, and the curing method may be selected as appropriate according to the use application.
- the cured product of the invention can be produced into a laminate by laminating the cured product with a base material.
- an inorganic material such as metal or glass; an organic material such as plastic or wood; and the like may be used as appropriate depending on the use application, and the shape of the laminate may be a flat plate, a sheet shape, or a three-dimensional shape having a three-dimensional structure. Any arbitrary shape according to the purpose, such as a shape having a curvature on the entire surface or a portion thereof, may be used. Furthermore, there are no limitations on the hardness, thickness, and the like of the base material. Furthermore, it is also acceptable that the cured product of the invention is used as a base material, and the cured product of the invention is further laminated thereon.
- a metal foil In the case of use applications such as a circuit board and a semiconductor package board, it is preferable to laminate a metal foil, and examples of the metal foil include copper foil, aluminum foil, gold foil, and silver foil. From the viewpoint of having satisfactory processability, it is preferable to use copper foil.
- the cured product layer may be formed by directly applying a composition on the base material, or by molding, and it is also acceptable to laminate a layer that has been molded in advance.
- the coating method is not particularly limited, and examples thereof include a spray method, a spin coating method, a dipping method, a roll coating method, a blade coating method, a doctor roll method, a doctor blade method, a curtain coating method, a slit coating method, a screen printing method, and an inkjet method.
- in-mold molding, insert molding, vacuum molding, extrusion lamination molding, press molding, and the like may be used.
- an uncured or semi-cured composition layer may be laminated and then cured, or a cured product layer obtained by completely curing the composition may be laminated on the base material.
- a precursor that can become a base material is laminated on the cured product of the invention by applying and curing the precursor, or the precursor that can become a base material or the composition of the invention may be adhered to the cured product of the invention in an uncured or semi-cured state and then may be cured.
- the precursor that can become a base material is not particularly limited, and various curable resin compositions may be used.
- the composition of the invention includes a fibrous substrate, and the fibrous substrate is a reinforcing fiber
- the composition including the fibrous substrate can be used as a fiber-reinforced resin.
- the method for incorporating a fibrous substrate into the composition is not particularly limited as long as the method does not impair the effects of the invention, and examples thereof include methods of compositizing the fibrous substrate and the composition by methods such as kneading, coating, impregnation, injection, and compression.
- the incorporation method can be selected as appropriate depending on the form of the fiber and the use application of the fiber-reinforced resin.
- the method for molding the fiber-reinforced resin of the invention is not particularly limited.
- an extrusion molding method is generally used; however, molding can also be achieved by flat surface pressing.
- a solution casting method can be used.
- examples thereof include inflation film molding, cast molding, extrusion lamination molding, calender molding, sheet molding, fiber molding, blow molding, injection molding, rotational molding, and coating molding.
- a cured product can be produced by using various curing methods using active energy rays.
- a molding method of producing a molding material into a prepreg and pressing and heating the prepreg using a press or an autoclave may be used.
- Resin Transfer Molding (RTM) molding, Vacuum assist Resin Transfer Molding (VaRTM) molding, lamination molding, hand lay-up molding, and the like may be used.
- the fiber-reinforced resin of the invention can form a state called an uncured or semi-cured prepreg.
- a cured product may also be formed by distributing a manufactured product in a prepreg state and then performing final curing.
- a laminate when a prepreg is formed, subsequently other layers are laminated thereon, and then final curing is performed, a laminate having various layers closely adhered to each other can be formed, which is preferable.
- the mass proportions of the composition and the fibrous substrate used at this time is not particularly limited; however, usually, it is preferable to adjust the resin fraction in the prepreg to be 20% to 60% by mass.
- the substituted or unsubstituted allyl group-containing maleimide compound of the invention is such that since the cured product thereof undergoes low linear expansion and has excellent resistance to thermal decomposition, the cured product can be suitably used for a heat-resistant member or an electronic member. Particularly, the cured product can be suitably used for a semiconductor encapsulating material, a circuit board, a buildup film, a buildup substrate, an adhesive, or a resist material. Furthermore, the substituted or unsubstituted allyl group-containing maleimide compound can also be suitably used for a matrix resin of the fiber-reinforced resin, and is particularly suitable as a highly heat-resistant prepreg.
- the maleimide compound exhibits solubility in various solvents, the maleimide compound can be produced into coating materials. Furthermore, since the maleimide compound can be cured at low temperature compared to conventional heat-resistant coating materials that require high-temperature baking at or above 300°C, the maleimide compound can also be suitably used as a resin for a heat-resistant coating material.
- a heat-resistant member or electronic member thus obtainable can be suitably used for various use applications, and examples of the applications include, but are not limited to, industrial machine parts, general machine parts, parts for automobiles, railways, vehicles, and the like, aerospace-related parts, electronic and electric parts, construction materials, container and packaging materials, daily goods, sports and leisure goods, and case members for wind power generation.
- a method for obtaining a semiconductor encapsulating material from the composition of the invention a method of sufficiently melting and mixing the above-mentioned composition, a curing accelerator, and compounding agents such as an inorganic filler, using an extruder, a kneader, rolls, or the like as necessary, until the mixture becomes uniform, may be used.
- fused silica is used as the inorganic filler; however, in a case in which the composition of the invention is used as a highly heat-conductive semiconductor encapsulating material for power transistors and power IC's, crystalline silica having higher thermal conductivity than fused silica, high-packaging fillers such as alumina and silicon nitride, or fused silica, crystalline silica, alumina, silicon nitride or the like may be used.
- the filling factor it is preferable to use an inorganic filler in an amount in the range of 30% to 95% by mass with respect to 100 parts by mass of the curable resin composition.
- the amount of the inorganic filler is more preferably 70 parts by mass or more, and even more preferably 80 parts by mass or more.
- a method of casting the semiconductor encapsulating material described above, or molding the semiconductor encapsulating material using a transfer molding machine, an injection molding machine, or the like, and heating the resultant at 50°C to 250°C for a time between 2 and 10 hours, may be mentioned.
- a method for laminating the above-mentioned prepreg by a conventional method, appropriately overlapping a copper foil, and heating and compressing the laminate at 170°C to 300°C at a pressure of 1 to 10 MPa for 10 minutes to 3 hours, may be mentioned.
- a method for obtaining a buildup substrate from the composition of the invention for example, the following steps may be mentioned.
- a step of applying the above-described composition, which has been produced by appropriately mixing rubber, a filler, or the like, on a circuit board having a circuit formed thereon using a spray coating method, a curtain coating method, or the like, and then curing the composition (Step 1).
- a step of subsequently performing perforation of predetermined through-holes and the like as necessary, subsequently treating the cured product with a roughening agent, forming concavities and convexities by rinsing the surface with hot water, and subjecting a metal such as copper to a plating treatment (Step 2).
- a step of sequentially repeating these operations as desired, and forming a resin insulating layer and a conductor layer of a predetermined circuit pattern by alternately building up the layers (Step 3).
- perforation of through-holes is performed after the formation of a resin insulating layer as the outermost layer.
- the buildup substrate of the invention can also be produced by compressing, under heating at 170°C to 300°C, a resin-attached copper foil obtained by semi-curing the resin composition on a copper foil, on a wiring board having a circuit formed thereon, while omitting a process of forming a roughened surface and subjecting the surface to a plating treatment.
- a buildup film can be produced by applying the above-described composition on the surface of a supporting film (Y) as a base material, drying the organic solvent by heating, blowing hot air, or the like, and thereby forming a layer (X) of the composition.
- ketones such as acetone, methyl ethyl ketone, and cyclohexanone; acetic acid esters such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate and carbitol acetate; carbitols such as cellosolve and butyl carbitol; aromatic hydrocarbons such as toluene and xylene; dimethylformamide, dimethylacetamide, N-methylpyrrolidone; and the like. Furthermore, it is preferable to use the organic solvent at a proportion that makes a non-volatile fraction of 30% to 60% by mass.
- the thickness of the layer (X) thus formed is usually adjusted to be greater than or equal to the thickness of the conductor layer. Since the thickness of the conductor layer carried by a circuit board is usually in the range of 5 to 70 ⁇ m, it is preferable that the thickness of the resin composition layer has a thickness of 10 to 100 ⁇ m.
- the layer (X) of the composition according to the invention may be protected with a protective film that will be mentioned below. By protecting the layer with a protective film, adhesion of contaminants or scratches to the resin composition layer surface can be prevented.
- the supporting film and the protective film described above include films of polyolefins such as polyethylene, polypropylene, and polyvinyl chloride; polyesters such as polyethylene terephthalate (hereinafter, may be abbreviated to "PET"), and polyethylene naphthalate; polycarbonate, and polyimide; as well as release paper, and metal foils such as copper foil and aluminum foil.
- PET polyethylene terephthalate
- the supporting film and the protective film may also be subjected to a release treatment in addition to a mad treatment and a corona treatment.
- the thickness of the supporting film is not particularly limited; however, the thickness is usually 10 to 150 ⁇ m, and preferably in the range of 25 to 50 ⁇ m. Furthermore, the thickness of the protective film is preferably set to 1 to 40 ⁇ m.
- the above-described supporting film (Y) is detached after the buildup film is laminated on a circuit board, or after an insulating layer is formed by heating and curing the composition.
- the supporting film (Y) is detached after a curable resin composition layer that constitutes the buildup film is heated and cured, adhesion of contaminants and the like during the curing process can be prevented.
- the supporting film is usually subjected to a release treatment in advance.
- a multilayer printed circuit board can be produced.
- the layer (X) is protected with a protective film, these layers are detached, and then the layer (X) is laminated on one surface or on both surfaces of a circuit board so as to come into direct contact with the circuit board, for example, by a vacuum lamination method.
- the method for lamination may be of batch type or of continuous type using rolls.
- the compression temperature lamination temperature
- the compression pressure 1 to 11 kgf/cm 2 (9.8 ⁇ 10 4 to 107.9 ⁇ 10 4 N/m 2 ). It is preferable to perform lamination under reduced pressure by setting the air pressure to be 20 mmHg (26.7 hPa) or less.
- a method for obtaining a conductive paste from the composition of the invention for example, a method of dispersing electroconductive particles in the composition may be mentioned.
- the conductive paste can be produced into a paste resin composition for circuit connection or an anisotropic conductive adhesive, depending on the type of the electroconductive particles used.
- HPLC high performance liquid chromatography
- MS spectroscopy MS spectroscopy
- DSC differential scanning calorimetry
- reaction product (a-1) was obtained.
- Allyl group-containing maleimide compound B was obtained by a method similar to that of Example 1, except that the hydroxy group-containing diamine represented by Formula (b) was used instead of BAHF, and the molar ratio was appropriately adjusted. Incidentally, the 1 H-NMR, 13 C-NMR, MS spectra, and DSC of the allyl group-containing maleimide compound B were measured, and the maleimide compound was subjected to HPLC to determine the purity. The following results were obtained.
- the reaction mixture was air-cooled to 80°C, and then the reaction liquid was neutralized with a 10% aqueous solution of sodium hydroxide.
- the neutralized reaction liquid was extracted with toluene.
- the extract was washed with ion-exchanged water and dried by adding sodium sulfate thereto.
- the residue was concentrated under reduced pressure, and thus a deep red-colored liquid was obtained.
- the liquid was dried in a vacuum for 12 hours at 80°C, and thus 105.41 g (yield 93.3%) of a dihydroxy group-containing nitro compound represented by the following Formula (c-0) was obtained as an orange-colored solid.
- a crude product of the allyl group-containing maleimide compound C was obtained by a method similar to that of Example 1, except that the molar ratio was appropriately adjusted by using the dihydroxy group-containing amino compound represented by Formula (c) instead of BAHF.
- the 1 H-NMR, 13 C-NMR, MS spectra, and DSC of the allyl group-containing maleimide compound A thus obtained were measured, and the maleimide compound was subjected to HPLC to determine the purity.
- the following results were obtained.
- a crude product of the allyl group-containing maleimide compound C was obtained by a method similar to that of Example 1, except that the molar ratio was appropriately adjusted by using the dihydroxy group-containing diamino compound represented by Formula (d) instead of BAHF.
- the 1 H-NMR, 13 C-NMR, MS spectra, and DSC of the allyl group-containing maleimide compound A thus obtained were measured, and the maleimide compound was subjected to HPLC to determine the purity. The following results were obtained.
- An allyl group-containing maleimide compound E was obtained by a method similar to that of Example 1, except that the molar ratio was appropriately adjusted by using the dihydroxy group-containing diamino compound represented by Formula (e) instead of BAHF.
- BMI-1000 (4,4'-diphenylmethanebismaleimide, manufactured by Daiwa Kasei Industry Co., Ltd.) represented by the following formula was used.
- a composition including a maleimide compound was produced, and the composition was cured to produce a cured product.
- compositions 1 to 8 were produced by mixing components according to the following Table 2. Furthermore, the compositions 1 to 8 thus obtained were cured under the following conditions, and cured products 1 to 8 were produced.
- compositions 4 to 6 and 8 when the cured products were produced, the compositions did not melt partially or entirely. Thus, cured products 4 to 6 and 8 could not be produced, and therefore, the evaluation of the glass transition temperature, linear expansion coefficient, and resistance to thermal decomposition could not be carried out.
- Each of the cured products 1 to 8 thus produced was cut out into a size of 5 mm in width and 5 mm in length, and this was used as a test specimen.
- the expansion rate in the range of 40°C to 60°C was measured using a thermomechanical analyzer ("TMA/SS7100" manufactured by Hitachi High-Technologies Corporation, rate of temperature increase: 3°C/min). The results thus obtained are presented in the following Table 3.
- compositions including a maleimide compound and glass fibers as a fibrous substrate were produced, and the compositions were cured to produce cured products.
- Compositions 9 to 16 were produced by mixing components according to the following Table 4. At this time, T-725H (glass fiber for molding materials, manufactured by Nippon Electric Glass Co., Ltd.) was used as a glass fiber.
- compositions 9 to 16 thus obtained were cured under the following conditions, and thus cured products 9 to 16 were produced.
- compositions 12 to 14 and 16 when cured products were produced, the compositions did not melt partially or entirely, and thus, cured products 12 to 14 and 16 could not be produced. Therefore, the evaluation of flexural modulus, bending strain, and bending strength could not be carried out.
- compositions including a maleimide compound and spherical silica as a filler were produced.
- compositions 17 to 24 were produced.
- FB-560 manufactured by Denka Company Limited
- KBM-403 y-glycidoxytriethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.
- PEARL WAX No. 1-P manufactured by CERARICA NODA Co., Ltd.
- compositions 20 to 22 and 24 did not melt at 175°C, and measurement of the spiral flow value could not be carried out.
- Table 7 Spiral flow value (cm) Composition 17 32 Composition 18 58 Composition 19 42 Composition 20 Not measurable Composition 21 Not measurable Composition 22 Not measurable Composition 23 38 Composition 24 Not measurable
- compositions including a maleimide compound and methyl ethyl ketone as an organic solvent were produced.
- the dielectric constant, dielectric loss tangent, and moisture-resistant solder resistance were evaluated.
- compositions 25 to 32 were produced by mixing components according to the following Table 8. At this time, the non-volatile fraction (N.V.) of the compositions thus obtainable was 58% by mass.
- compositions 25 to 32 thus obtained were cured under the following conditions, and laminates 25 to 32 having a base material and a layer containing a cured product were produced.
- compositions 28 to 32 since the compositions were poorly soluble in methyl ethyl ketone, and cured products could not be produced, the evaluation of the dielectric constant, dielectric loss tangent, and moisture-resistant solder resistance could not be carried out.
- compositions including a maleimide compound and a photopolymerization initiator were produced.
- Compositions 33 to 40 were produced by mixing components according to the following Table 10. At this time, IRGACURE 907 (2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-1-propanon e, manufactured by BASF SE) was used as a photopolymerization initiator.
- compositions 36 to 40 had poor compatibility with photopolymerization initiator M-309 (trimethylolpropane triacrylate (TMPTA), manufactured by TOAGOSEI CO., LTD.), and the compositions could not be produced. Therefore, curability could not be evaluated.
- photopolymerization initiator M-309 trimethylolpropane triacrylate (TMPTA), manufactured by TOAGOSEI CO., LTD.
- composition was applied on a glass substrate to a thickness of 50 ⁇ m.
- the composition was irradiated with ultraviolet radiation at a dose starting from 50 mJ/cm 2 at an increment of 10 mJ/cm 2 , and the cumulative amount of light until the coating film surface became tack-free was measured.
- Table 11 Cumulative amount of light (mJ/cm 2 ) Composition 33 120 Composition 34 90 Composition 35 130 Composition 36 Not measurable Composition 37 Not measurable Composition 38 Not measurable Composition 39 Not measurable Composition 40 Not measurable
- compositions including a maleimide compound and methyl ethyl ketone as an organic solvent were produced.
- compositions 41 to 48 were produced by mixing components according to the following Table 12. At this time, the non-volatile fraction (N.V.) of the compositions thus obtainable was 40% by mass.
- a composition was applied on a base material such that the thickness after curing would be 20 ⁇ m, and the composition was cured for 2 hours at 250°C.
- the external appearance was visually observed and evaluated according to the following criteria.
- the results thus obtained are presented in the following Table 13.
- a standard stainless steel plate SUS-304 was used.
- the substituted or unsubstituted allyl group-containing maleimide compound of the invention is such that a cured product thereof undergoes low linear expansion and has excellent resistance to thermal decomposition. Therefore, the compound can be used suitably for a heat-resistant member or an electronic member. Particularly, the compound can be used suitably for a semiconductor encapsulating material, a circuit board, a buildup film, a buildup substrate, an adhesive, or a resist material. The compound can also be used suitably for a matrix resin of a fiber-reinforced resin, and is particularly suitable as a highly heat-resistant prepreg. Furthermore, since the compound exhibits photocurability, the compound can be suitably for various photocurable molding materials, and since compound exhibits film-forming properties, the compound can be suitably used as a resin for a heat-resistant coating material.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pyrrole Compounds (AREA)
- Reinforced Plastic Materials (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2016111865 | 2016-06-03 | ||
PCT/JP2017/020418 WO2017209236A1 (ja) | 2016-06-03 | 2017-06-01 | 置換または非置換アリル基含有マレイミド化合物およびその製造方法、並びに前記化合物を用いた組成物および硬化物 |
Publications (2)
Publication Number | Publication Date |
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EP3466925A1 true EP3466925A1 (de) | 2019-04-10 |
EP3466925A4 EP3466925A4 (de) | 2019-11-13 |
Family
ID=60478806
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP17806786.4A Withdrawn EP3466925A4 (de) | 2016-06-03 | 2017-06-01 | Substituierte oder unsubstituierte allylgruppe enthaltende maleimidverbindung, herstellungsverfahren dafür sowie zusammensetzung und gehärtetes produkt mit verwendung der besagten verbindung |
Country Status (7)
Country | Link |
---|---|
US (1) | US10981865B2 (de) |
EP (1) | EP3466925A4 (de) |
JP (1) | JP6939780B2 (de) |
KR (1) | KR102320490B1 (de) |
CN (1) | CN109219593B (de) |
TW (1) | TWI737743B (de) |
WO (1) | WO2017209236A1 (de) |
Cited By (1)
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CN114621559A (zh) * | 2020-12-09 | 2022-06-14 | 广东生益科技股份有限公司 | 一种热固性树脂组合物及包含其的预浸料、层压板和高频电路基板 |
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US11104788B2 (en) * | 2016-12-20 | 2021-08-31 | Dic Corporation | Composition, cured product and laminate |
KR20200128008A (ko) * | 2018-02-28 | 2020-11-11 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 화합물, 수지, 조성물 및 그것을 이용한 리소그래피용 막형성재료 |
JP7434886B2 (ja) * | 2019-12-25 | 2024-02-21 | Dic株式会社 | (メタ)アクリレート樹脂組成物、硬化性樹脂組成物、硬化物及び物品 |
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JP2022108927A (ja) * | 2021-01-14 | 2022-07-27 | 味の素株式会社 | 樹脂組成物 |
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-
2017
- 2017-06-01 US US16/304,875 patent/US10981865B2/en active Active
- 2017-06-01 JP JP2018520991A patent/JP6939780B2/ja active Active
- 2017-06-01 WO PCT/JP2017/020418 patent/WO2017209236A1/ja unknown
- 2017-06-01 CN CN201780034469.9A patent/CN109219593B/zh active Active
- 2017-06-01 EP EP17806786.4A patent/EP3466925A4/de not_active Withdrawn
- 2017-06-01 KR KR1020187034640A patent/KR102320490B1/ko active IP Right Grant
- 2017-06-03 TW TW106118378A patent/TWI737743B/zh active
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114621559A (zh) * | 2020-12-09 | 2022-06-14 | 广东生益科技股份有限公司 | 一种热固性树脂组合物及包含其的预浸料、层压板和高频电路基板 |
WO2022120920A1 (zh) * | 2020-12-09 | 2022-06-16 | 广东生益科技股份有限公司 | 一种热固性树脂组合物及包含其的预浸料、层压板和高频电路基板 |
CN114621559B (zh) * | 2020-12-09 | 2023-07-11 | 广东生益科技股份有限公司 | 一种热固性树脂组合物及包含其的预浸料、层压板和高频电路基板 |
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TWI737743B (zh) | 2021-09-01 |
TW201819359A (zh) | 2018-06-01 |
JPWO2017209236A1 (ja) | 2019-03-28 |
EP3466925A4 (de) | 2019-11-13 |
JP6939780B2 (ja) | 2021-09-22 |
KR102320490B1 (ko) | 2021-11-02 |
CN109219593A (zh) | 2019-01-15 |
US10981865B2 (en) | 2021-04-20 |
KR20190015258A (ko) | 2019-02-13 |
WO2017209236A1 (ja) | 2017-12-07 |
CN109219593B (zh) | 2022-04-22 |
US20200325101A1 (en) | 2020-10-15 |
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